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Synlett 2006(18): 2953-2958
DOI: 10.1055/s-2006-951512
DOI: 10.1055/s-2006-951512
LETTER
© Georg Thieme Verlag Stuttgart · New YorkSolvent-Free, Open-Vessel Microwave-Promoted Heck Couplings: From the mmol to the mol Scale
Weitere Informationen
Received
10 May 2006
Publikationsdatum:
25. Oktober 2006 (online)
Publikationsverlauf
Publikationsdatum:
25. Oktober 2006 (online)
Abstract
The rapid, microwave-promoted Heck coupling of aryl iodides in open reaction vessels is presented and scale-up of the reactions to the mol scale demonstrated. Reactions are performed using 0.1 mol% palladium acetate as the catalyst, sodium carbonate and tributylamine as bases and tetrabutylammonium bromide as an additive.
Key words
palladium - Heck reaction - catalysis - solvent-free - microwave
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It is important that a suitably sized reaction vessel is used for scale-up reactions in the absence of solvent. It is advised that the contents should occupy no more than 10% of the vessel volume. In addition, microwave power should be carefully modulated. A power no greater than 600 W is advised.
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At a first glance it may seem that this would be putting in much more microwave power than in the case of the monomode experiments. However, the relative size of the cavity needs to be considered. Multimode microwaves have large cavities and so power is dissipated over a large area. Monomode equipment has a much smaller cavity and the energy density is up to some 30-40 times higher than the multimode apparatus.
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References and Notes
It is more appropriate to call the Pd(OAc)2 a precatalyst since a colloidal palladium species is most likely the catalytically active species.